I'm not sure how to begin debugging. Taking a look at the server.log and console.log files shows nothing happening differently during this time period.
If you need more information, I'll gladly provide. I don't even really know where to begin looking so I apologize if this post is light on information.
EDIT: On closer inspection, I found that the files which begin to 404 are all inside subdirectories of the deployed WAR file. I'm not sure what the relevance is.
As the situation goes, it appears to be:
1) Site is okay.
2) Something happens.
4) Files in subdirectories of webapp can no longer be retrieved
The structure of the webapp looks like: myWebApp.war
Any file contained in the js and images directory can't be retrieved anymore if/when this problem occurs. I'm decently sure that the problem also makes files in META-INF and WEB-INF unreachable since none of my servlets got called when I checked my copy of the attempted load. The jsp files work just fine though.
What's more, because the site will not function until JBoss restarts, I'm fairly certain something involved in searching through subdirectories crashed. I have no idea what that could be.
Would it be possible that this could be fixed by extracting the contents of the war file?